[2,7-Dihy-droxy-8-(4-phen-oxy-benzo-yl)naphthalen-1-yl](4-phen-oxy-phen-yl)methanone.

In the title compound, C(36)H(24)O(6), the benzoyl groups at the 1- and 8-positions of the naphthalene system are in an anti orientation. Both carbonyl groups form intra-molecular O-H⋯O hydrogen bonds with hy-droxy groups affording six-membered rings. The benzene rings of the benzoyl groups make dihedral angles of 59.26 (13) and 59.09 (13)° with the naphthalene ring system. Zigzag C-H⋯O chains and ladder C-H⋯O chains between the phenoxybenzoyl groups along the ab diagonals form an undulating checkered sheet. The molecules are further connected into a three-dimensional network by C-H⋯π interactions.

Related literature

For electrophilic aromatic aroylation of the naphthalene core, see: Okamoto & Yonezawa (2009 ▶); Okamoto et al. (2011 ▶, 2013 ▶). For the structures of (2,7-dimeth­oxy­naphthalene-1,8-di­yl)bis­(4-fluoro­phen­yl)di­meth­anone and 2,7-dimeth­oxy-1,8-bis­(4-phen­oxy­benzo­yl)naphthalene, see: Watanabe et al. (2010 ▶) andr Hijikata et al. (2010 ▶), respectively.

Experimental

Crystal data

C36H24O6

M = 552.55

Monoclinic,

a = 16.0313 (3) Å

b = 18.4956 (3) Å

c = 12.1238 (2) Å

β = 131.389 (1)°

V = 2696.95 (9) Å3

Z = 4

Cu Kα radiation

μ = 0.75 mm−1

T = 193 K

0.60 × 0.55 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.661, T max = 0.929

22236 measured reflections

4868 independent reflections

4527 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.096

S = 1.08

4868 reflections

382 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 2389 Friedel pairs

Flack parameter: 0.05 (19)

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: Il Milione (Burla et al., 2007 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812052038/rn2112sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812052038/rn2112Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812052038/rn2112Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C36H24O6	F(000) = 1152
Mr = 552.55	Dx = 1.361 Mg m−3
Monoclinic, Cc	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: C -2yc	Cell parameters from 14515 reflections
a = 16.0313 (3) Å	θ = 4.4–68.1°
b = 18.4956 (3) Å	µ = 0.75 mm−1
c = 12.1238 (2) Å	T = 193 K
β = 131.389 (1)°	Block, yellow
V = 2696.95 (9) Å3	0.60 × 0.55 × 0.10 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	4868 independent reflections
Radiation source: rotating anode	4527 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 10.000 pixels mm-1	θmax = 68.1°, θmin = 4.4°
ω scans	h = −19→19
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −22→22
Tmin = 0.661, Tmax = 0.929	l = −14→14
22236 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.037	w = 1/[σ2(Fo2) + (0.0414P)2 + 1.2872P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.20 e Å−3
4868 reflections	Δρmin = −0.21 e Å−3
382 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraints	Extinction coefficient: 0.00222 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2389 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.05 (19)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.46616 (15)	0.24827 (8)	0.4776 (2)	0.0586 (5)
O2	0.36810 (15)	0.00189 (8)	0.4778 (2)	0.0589 (5)
O3	0.78626 (13)	−0.00972 (9)	0.69269 (17)	0.0540 (4)
O4	0.26329 (13)	0.25987 (9)	0.69275 (17)	0.0540 (4)
O5	0.3598 (2)	0.31569 (12)	0.2334 (3)	0.0889 (7)
H5A	0.4028	0.3117	0.3252	0.107*
O6	0.2301 (2)	−0.06560 (12)	0.2333 (3)	0.0887 (7)
H6A	0.2881	−0.0652	0.3226	0.106*
C1	0.33277 (19)	0.18893 (13)	0.2506 (2)	0.0461 (5)
C2	0.3049 (3)	0.25255 (17)	0.1699 (3)	0.0664 (8)
C3	0.2213 (3)	0.2516 (3)	0.0165 (4)	0.0985 (15)
H3	0.2020	0.2950	−0.0374	0.118*
C4	0.1684 (3)	0.1906 (3)	−0.0546 (3)	0.1016 (16)
H4	0.1154	0.1909	−0.1591	0.122*
C5	0.1337 (2)	0.0591 (3)	−0.0547 (3)	0.1027 (16)
H5	0.0822	0.0587	−0.1592	0.123*
C6	0.1529 (3)	−0.0033 (3)	0.0189 (4)	0.1012 (15)
H6	0.1190	−0.0471	−0.0339	0.121*
C7	0.2216 (2)	−0.00274 (17)	0.1702 (3)	0.0661 (8)
C8	0.27453 (17)	0.06111 (13)	0.2507 (2)	0.0460 (5)
C9	0.26698 (17)	0.12502 (15)	0.1775 (2)	0.0487 (5)
C10	0.1889 (2)	0.1250 (2)	0.0211 (3)	0.0757 (9)
C11	0.43775 (19)	0.19208 (11)	0.4067 (2)	0.0426 (5)
C12	0.51884 (16)	0.13161 (11)	0.4748 (2)	0.0369 (4)
C13	0.59891 (17)	0.12824 (12)	0.6275 (2)	0.0422 (5)
H13	0.5936	0.1599	0.6843	0.051*
C14	0.68556 (17)	0.07991 (13)	0.6977 (2)	0.0452 (5)
H14	0.7375	0.0764	0.8019	0.054*
C15	0.69610 (16)	0.03646 (11)	0.6145 (2)	0.0399 (4)
C16	0.61693 (17)	0.03743 (12)	0.4626 (2)	0.0413 (5)
H16	0.6240	0.0065	0.4066	0.050*
C17	0.52707 (17)	0.08406 (12)	0.3929 (2)	0.0405 (5)
H17	0.4707	0.0836	0.2888	0.049*
C18	0.32565 (17)	0.05816 (11)	0.4067 (2)	0.0427 (5)
C19	0.31261 (16)	0.11833 (11)	0.4748 (2)	0.0368 (4)
C20	0.38516 (17)	0.12173 (12)	0.6276 (2)	0.0421 (5)
H20	0.4471	0.0899	0.6844	0.050*
C21	0.36894 (18)	0.17017 (13)	0.6976 (2)	0.0458 (5)
H21	0.4215	0.1738	0.8018	0.055*
C22	0.27547 (17)	0.21371 (11)	0.6151 (2)	0.0399 (4)
C23	0.20247 (17)	0.21294 (12)	0.4623 (2)	0.0412 (5)
H23	0.1397	0.2441	0.4063	0.049*
C24	0.22251 (17)	0.16599 (12)	0.3928 (2)	0.0402 (5)
H24	0.1746	0.1662	0.2886	0.048*
C25	0.83934 (16)	−0.02601 (13)	0.6401 (2)	0.0449 (5)
C26	0.87387 (19)	−0.09629 (14)	0.6575 (3)	0.0530 (6)
H26	0.8565	−0.1317	0.6964	0.064*
C27	0.9345 (2)	−0.11477 (15)	0.6174 (3)	0.0567 (6)
H27	0.9577	−0.1634	0.6274	0.068*
C28	0.9614 (2)	−0.06375 (15)	0.5636 (3)	0.0553 (6)
H28	1.0036	−0.0769	0.5372	0.066*
C29	0.92693 (19)	0.00719 (15)	0.5477 (3)	0.0532 (6)
H29	0.9457	0.0428	0.5108	0.064*
C30	0.86529 (18)	0.02621 (13)	0.5855 (2)	0.0480 (5)
H30	0.8410	0.0747	0.5740	0.058*
C31	0.15740 (18)	0.27605 (13)	0.6400 (2)	0.0447 (5)
C32	0.1402 (2)	0.34624 (14)	0.6574 (3)	0.0536 (6)
H32	0.1966	0.3815	0.6966	0.064*
C33	0.0399 (2)	0.36505 (15)	0.6174 (3)	0.0565 (6)
H33	0.0268	0.4137	0.6274	0.068*
C34	−0.0414 (2)	0.31361 (15)	0.5632 (3)	0.0553 (6)
H34	−0.1098	0.3267	0.5370	0.066*
C35	−0.0229 (2)	0.24338 (15)	0.5473 (3)	0.0536 (6)
H35	−0.0788	0.2079	0.5097	0.064*
C36	0.0773 (2)	0.22397 (13)	0.5859 (2)	0.0480 (5)
H36	0.0902	0.1754	0.5751	0.058*

	U11	U22	U33	U12	U13	U23
O1	0.0674 (11)	0.0398 (8)	0.0723 (11)	0.0032 (8)	0.0477 (10)	−0.0045 (8)
O2	0.0679 (12)	0.0406 (9)	0.0727 (11)	0.0090 (8)	0.0484 (10)	0.0052 (8)
O3	0.0489 (9)	0.0693 (11)	0.0468 (8)	0.0229 (8)	0.0329 (8)	0.0118 (7)
O4	0.0441 (9)	0.0691 (11)	0.0456 (8)	0.0075 (8)	0.0284 (7)	−0.0114 (7)
O5	0.1121 (19)	0.0656 (13)	0.1298 (19)	0.0416 (13)	0.0974 (18)	0.0511 (13)
O6	0.0801 (15)	0.0650 (13)	0.1276 (19)	−0.0250 (11)	0.0715 (14)	−0.0503 (13)
C1	0.0473 (12)	0.0584 (14)	0.0462 (12)	0.0211 (10)	0.0368 (11)	0.0146 (10)
C2	0.0748 (18)	0.0779 (19)	0.0782 (18)	0.0407 (15)	0.0640 (17)	0.0389 (15)
C3	0.081 (2)	0.161 (4)	0.080 (2)	0.077 (3)	0.064 (2)	0.080 (3)
C4	0.0517 (18)	0.217 (5)	0.0412 (15)	0.054 (3)	0.0328 (14)	0.038 (2)
C5	0.0345 (14)	0.219 (5)	0.0422 (15)	0.004 (2)	0.0201 (13)	−0.042 (2)
C6	0.0496 (17)	0.167 (4)	0.082 (2)	−0.031 (2)	0.0411 (18)	−0.083 (3)
C7	0.0424 (13)	0.080 (2)	0.0774 (18)	−0.0113 (13)	0.0403 (14)	−0.0387 (15)
C8	0.0302 (10)	0.0581 (14)	0.0470 (12)	0.0028 (9)	0.0244 (9)	−0.0147 (10)
C9	0.0329 (11)	0.0798 (15)	0.0347 (10)	0.0158 (11)	0.0230 (9)	−0.0004 (11)
C10	0.0336 (12)	0.159 (3)	0.0319 (11)	0.0234 (16)	0.0206 (10)	−0.0003 (16)
C11	0.0501 (12)	0.0401 (11)	0.0516 (12)	0.0021 (9)	0.0396 (11)	0.0009 (9)
C12	0.0329 (10)	0.0386 (10)	0.0411 (10)	−0.0010 (8)	0.0252 (9)	−0.0009 (8)
C13	0.0372 (11)	0.0491 (11)	0.0418 (10)	−0.0025 (9)	0.0269 (10)	−0.0094 (9)
C14	0.0351 (11)	0.0609 (13)	0.0352 (10)	0.0035 (9)	0.0213 (9)	−0.0013 (9)
C15	0.0341 (10)	0.0437 (11)	0.0426 (10)	0.0057 (9)	0.0257 (9)	0.0040 (9)
C16	0.0405 (11)	0.0445 (11)	0.0421 (10)	0.0030 (9)	0.0287 (9)	−0.0050 (8)
C17	0.0346 (10)	0.0504 (12)	0.0362 (10)	0.0050 (9)	0.0232 (9)	0.0013 (8)
C18	0.0355 (10)	0.0386 (11)	0.0523 (12)	0.0013 (9)	0.0283 (10)	−0.0003 (9)
C19	0.0377 (10)	0.0384 (10)	0.0410 (10)	0.0008 (8)	0.0289 (9)	0.0017 (8)
C20	0.0385 (11)	0.0489 (11)	0.0418 (10)	0.0101 (9)	0.0278 (9)	0.0092 (9)
C21	0.0400 (11)	0.0627 (13)	0.0346 (10)	0.0052 (10)	0.0247 (9)	0.0016 (9)
C22	0.0392 (11)	0.0460 (11)	0.0404 (10)	0.0016 (9)	0.0289 (9)	−0.0025 (9)
C23	0.0379 (10)	0.0450 (11)	0.0405 (10)	0.0104 (9)	0.0259 (9)	0.0054 (8)
C24	0.0350 (11)	0.0509 (12)	0.0360 (10)	0.0034 (9)	0.0241 (9)	−0.0008 (8)
C25	0.0310 (10)	0.0608 (14)	0.0350 (10)	0.0065 (9)	0.0184 (9)	−0.0036 (9)
C26	0.0390 (12)	0.0598 (14)	0.0540 (13)	0.0056 (10)	0.0281 (11)	−0.0001 (11)
C27	0.0425 (12)	0.0593 (15)	0.0600 (14)	0.0066 (11)	0.0303 (11)	−0.0098 (12)
C28	0.0370 (11)	0.0753 (16)	0.0529 (12)	−0.0033 (11)	0.0294 (11)	−0.0173 (12)
C29	0.0395 (12)	0.0713 (16)	0.0431 (12)	−0.0088 (11)	0.0248 (10)	−0.0100 (11)
C30	0.0368 (11)	0.0516 (13)	0.0411 (11)	0.0009 (9)	0.0196 (10)	−0.0073 (9)
C31	0.0428 (11)	0.0600 (14)	0.0358 (10)	0.0109 (10)	0.0280 (10)	0.0043 (9)
C32	0.0589 (15)	0.0611 (14)	0.0552 (13)	0.0054 (11)	0.0439 (13)	0.0000 (11)
C33	0.0672 (16)	0.0597 (15)	0.0581 (14)	0.0193 (13)	0.0481 (13)	0.0102 (11)
C34	0.0507 (13)	0.0771 (17)	0.0521 (12)	0.0203 (13)	0.0400 (11)	0.0176 (12)
C35	0.0514 (14)	0.0697 (16)	0.0444 (12)	0.0038 (12)	0.0336 (11)	0.0090 (11)
C36	0.0547 (13)	0.0530 (13)	0.0417 (11)	0.0106 (10)	0.0342 (11)	0.0075 (9)

O1—C11	1.228 (3)	C16—H16	0.9500
O2—C18	1.230 (3)	C17—H17	0.9500
O3—C15	1.380 (2)	C18—C19	1.481 (3)
O3—C25	1.392 (3)	C19—C20	1.393 (3)
O4—C22	1.377 (2)	C19—C24	1.397 (3)
O4—C31	1.395 (3)	C20—C21	1.372 (3)
O5—C2	1.355 (4)	C20—H20	0.9500
O5—H5A	0.8400	C21—C22	1.383 (3)
O6—C7	1.348 (4)	C21—H21	0.9500
O6—H6A	0.8400	C22—C23	1.391 (3)
C1—C2	1.401 (3)	C23—C24	1.387 (3)
C1—C9	1.435 (4)	C23—H23	0.9500
C1—C11	1.485 (3)	C24—H24	0.9500
C2—C3	1.399 (5)	C25—C26	1.373 (3)
C3—C4	1.329 (6)	C25—C30	1.382 (3)
C3—H3	0.9500	C26—C27	1.387 (4)
C4—C10	1.423 (6)	C26—H26	0.9500
C4—H4	0.9500	C27—C28	1.370 (4)
C5—C6	1.364 (6)	C27—H27	0.9500
C5—C10	1.428 (6)	C28—C29	1.387 (4)
C5—H5	0.9500	C28—H28	0.9500
C6—C7	1.381 (5)	C29—C30	1.381 (3)
C6—H6	0.9500	C29—H29	0.9500
C7—C8	1.404 (3)	C30—H30	0.9500
C8—C9	1.435 (4)	C31—C32	1.372 (3)
C8—C18	1.484 (3)	C31—C36	1.376 (3)
C9—C10	1.422 (3)	C32—C33	1.383 (4)
C11—C12	1.484 (3)	C32—H32	0.9500
C12—C13	1.392 (3)	C33—C34	1.379 (4)
C12—C17	1.396 (3)	C33—H33	0.9500
C13—C14	1.375 (3)	C34—C35	1.374 (4)
C13—H13	0.9500	C34—H34	0.9500
C14—C15	1.385 (3)	C35—C36	1.390 (3)
C14—H14	0.9500	C35—H35	0.9500
C15—C16	1.383 (3)	C36—H36	0.9500
C16—C17	1.387 (3)
C15—O3—C25	119.93 (16)	O2—C18—C8	120.5 (2)
C22—O4—C31	119.97 (16)	C19—C18—C8	121.35 (18)
C2—O5—H5A	109.5	C20—C19—C24	118.61 (18)
C7—O6—H6A	109.5	C20—C19—C18	118.29 (18)
C2—C1—C9	119.7 (2)	C24—C19—C18	122.58 (18)
C2—C1—C11	115.2 (2)	C21—C20—C19	121.27 (19)
C9—C1—C11	124.8 (2)	C21—C20—H20	119.4
O5—C2—C3	117.3 (3)	C19—C20—H20	119.4
O5—C2—C1	122.7 (3)	C20—C21—C22	119.41 (19)
C3—C2—C1	120.0 (3)	C20—C21—H21	120.3
C4—C3—C2	120.9 (3)	C22—C21—H21	120.3
C4—C3—H3	119.6	O4—C22—C21	116.27 (18)
C2—C3—H3	119.6	O4—C22—C23	122.82 (18)
C3—C4—C10	121.9 (3)	C21—C22—C23	120.80 (18)
C3—C4—H4	119.1	C24—C23—C22	119.10 (19)
C10—C4—H4	119.1	C24—C23—H23	120.4
C6—C5—C10	121.7 (3)	C22—C23—H23	120.4
C6—C5—H5	119.2	C23—C24—C19	120.58 (18)
C10—C5—H5	119.2	C23—C24—H24	119.7
C5—C6—C7	120.0 (3)	C19—C24—H24	119.7
C5—C6—H6	120.0	C26—C25—C30	121.1 (2)
C7—C6—H6	120.0	C26—C25—O3	116.2 (2)
O6—C7—C6	116.1 (3)	C30—C25—O3	122.5 (2)
O6—C7—C8	122.9 (3)	C25—C26—C27	119.0 (2)
C6—C7—C8	121.0 (4)	C25—C26—H26	120.5
C7—C8—C9	119.8 (2)	C27—C26—H26	120.5
C7—C8—C18	115.2 (2)	C28—C27—C26	120.8 (2)
C9—C8—C18	124.7 (2)	C28—C27—H27	119.6
C10—C9—C8	117.7 (3)	C26—C27—H27	119.6
C10—C9—C1	117.6 (3)	C27—C28—C29	119.7 (2)
C8—C9—C1	124.71 (18)	C27—C28—H28	120.2
C9—C10—C4	119.0 (3)	C29—C28—H28	120.2
C9—C10—C5	118.9 (3)	C30—C29—C28	120.2 (2)
C4—C10—C5	122.1 (3)	C30—C29—H29	119.9
O1—C11—C12	117.7 (2)	C28—C29—H29	119.9
O1—C11—C1	120.6 (2)	C29—C30—C25	119.3 (2)
C12—C11—C1	121.13 (18)	C29—C30—H30	120.4
C13—C12—C17	118.70 (18)	C25—C30—H30	120.4
C13—C12—C11	118.15 (18)	C32—C31—C36	121.1 (2)
C17—C12—C11	122.61 (18)	C32—C31—O4	116.1 (2)
C14—C13—C12	121.21 (19)	C36—C31—O4	122.6 (2)
C14—C13—H13	119.4	C31—C32—C33	119.3 (2)
C12—C13—H13	119.4	C31—C32—H32	120.3
C13—C14—C15	119.11 (19)	C33—C32—H32	120.3
C13—C14—H14	120.4	C34—C33—C32	120.4 (2)
C15—C14—H14	120.4	C34—C33—H33	119.8
O3—C15—C16	123.03 (18)	C32—C33—H33	119.8
O3—C15—C14	115.80 (18)	C35—C34—C33	119.7 (2)
C16—C15—C14	121.08 (18)	C35—C34—H34	120.1
C15—C16—C17	119.23 (19)	C33—C34—H34	120.1
C15—C16—H16	120.4	C34—C35—C36	120.3 (2)
C17—C16—H16	120.4	C34—C35—H35	119.8
C16—C17—C12	120.47 (18)	C36—C35—H35	119.8
C16—C17—H17	119.8	C31—C36—C35	119.1 (2)
C12—C17—H17	119.8	C31—C36—H36	120.5
O2—C18—C19	117.5 (2)	C35—C36—H36	120.5
C9—C1—C2—O5	176.4 (2)	O3—C15—C16—C17	178.0 (2)
C11—C1—C2—O5	−9.4 (3)	C14—C15—C16—C17	1.6 (3)
C9—C1—C2—C3	−7.1 (3)	C15—C16—C17—C12	2.6 (3)
C11—C1—C2—C3	167.1 (2)	C13—C12—C17—C16	−3.8 (3)
O5—C2—C3—C4	175.7 (3)	C11—C12—C17—C16	167.6 (2)
C1—C2—C3—C4	−1.0 (4)	C7—C8—C18—O2	34.8 (3)
C2—C3—C4—C10	4.1 (5)	C9—C8—C18—O2	−151.6 (2)
C10—C5—C6—C7	4.3 (5)	C7—C8—C18—C19	−135.9 (2)
C5—C6—C7—O6	175.6 (3)	C9—C8—C18—C19	37.8 (3)
C5—C6—C7—C8	−1.4 (4)	O2—C18—C19—C20	26.1 (3)
O6—C7—C8—C9	176.5 (2)	C8—C18—C19—C20	−163.0 (2)
C6—C7—C8—C9	−6.7 (3)	O2—C18—C19—C24	−145.5 (2)
O6—C7—C8—C18	−9.5 (3)	C8—C18—C19—C24	25.5 (3)
C6—C7—C8—C18	167.4 (2)	C24—C19—C20—C21	0.5 (3)
C7—C8—C9—C10	11.6 (3)	C18—C19—C20—C21	−171.4 (2)
C18—C8—C9—C10	−161.8 (2)	C19—C20—C21—C22	3.6 (3)
C7—C8—C9—C1	−168.3 (2)	C31—O4—C22—C21	−146.0 (2)
C18—C8—C9—C1	18.3 (3)	C31—O4—C22—C23	37.7 (3)
C2—C1—C9—C10	11.7 (3)	C20—C21—C22—O4	178.6 (2)
C11—C1—C9—C10	−161.8 (2)	C20—C21—C22—C23	−5.0 (3)
C2—C1—C9—C8	−168.4 (2)	O4—C22—C23—C24	178.3 (2)
C11—C1—C9—C8	18.0 (3)	C21—C22—C23—C24	2.1 (3)
C8—C9—C10—C4	171.4 (2)	C22—C23—C24—C19	2.1 (3)
C1—C9—C10—C4	−8.7 (3)	C20—C19—C24—C23	−3.5 (3)
C8—C9—C10—C5	−8.7 (3)	C18—C19—C24—C23	168.1 (2)
C1—C9—C10—C5	171.2 (2)	C15—O3—C25—C26	−140.9 (2)
C3—C4—C10—C9	0.9 (4)	C15—O3—C25—C30	44.7 (3)
C3—C4—C10—C5	−178.9 (3)	C30—C25—C26—C27	−0.8 (3)
C6—C5—C10—C9	0.9 (4)	O3—C25—C26—C27	−175.3 (2)
C6—C5—C10—C4	−179.2 (3)	C25—C26—C27—C28	1.1 (4)
C2—C1—C11—O1	34.9 (3)	C26—C27—C28—C29	−0.5 (4)
C9—C1—C11—O1	−151.3 (2)	C27—C28—C29—C30	−0.3 (3)
C2—C1—C11—C12	−136.1 (2)	C28—C29—C30—C25	0.5 (3)
C9—C1—C11—C12	37.7 (3)	C26—C25—C30—C29	0.0 (3)
O1—C11—C12—C13	26.0 (3)	O3—C25—C30—C29	174.1 (2)
C1—C11—C12—C13	−162.8 (2)	C22—O4—C31—C32	−141.1 (2)
O1—C11—C12—C17	−145.5 (2)	C22—O4—C31—C36	44.7 (3)
C1—C11—C12—C17	25.8 (3)	C36—C31—C32—C33	−1.2 (3)
C17—C12—C13—C14	0.8 (3)	O4—C31—C32—C33	−175.38 (19)
C11—C12—C13—C14	−171.0 (2)	C31—C32—C33—C34	1.2 (3)
C12—C13—C14—C15	3.3 (3)	C32—C33—C34—C35	−0.7 (4)
C25—O3—C15—C16	37.3 (3)	C33—C34—C35—C36	0.2 (3)
C25—O3—C15—C14	−146.1 (2)	C32—C31—C36—C35	0.6 (3)
C13—C14—C15—O3	178.8 (2)	O4—C31—C36—C35	174.45 (19)
C13—C14—C15—C16	−4.5 (3)	C34—C35—C36—C31	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O1	0.84	1.83	2.560 (3)	145
O6—H6A···O2	0.84	1.88	2.563 (3)	138
C26—H26···O4i	0.95	2.48	3.377 (4)	157
C27—H27···O1i	0.95	2.51	3.269 (4)	137
C32—H32···O3ii	0.95	2.49	3.382 (4)	156
C33—H33···O2ii	0.95	2.51	3.270 (4)	137
C14—H14···Cg1iii	0.95	2.80	3.740 (2)	171
C21—H21···Cg2iv	0.95	2.80	3.740 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C25—C30 and C31—C36 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O1	0.84	1.83	2.560 (3)	145
O6—H6A⋯O2	0.84	1.88	2.563 (3)	138
C26—H26⋯O4i	0.95	2.48	3.377 (4)	157
C27—H27⋯O1i	0.95	2.51	3.269 (4)	137
C32—H32⋯O3ii	0.95	2.49	3.382 (4)	156
C33—H33⋯O2ii	0.95	2.51	3.270 (4)	137
C14—H14⋯Cg1iii	0.95	2.80	3.740 (2)	171
C21—H21⋯Cg2iv	0.95	2.80	3.740 (2)	171

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .